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Rob Walling

๐Ÿ‘ค Speaker
3342 total appearances

Appearances Over Time

Podcast Appearances

Startups For the Rest of Us
Episode 762 | Doing Great Work, Hierarchy of SaaS Skills, and Public Deadlines (A Rob Solo Adventure)

So we jumped into a conference room and it was just like panic DEF CON 5 type thing. And it was Derek, myself, and I believe it was Anna, who was our customer success person. And we said, what do we need to change? And we spent like an hour just hashing out, what can we do to make this work? And then we pulled in a different engineer, Ian, off of the tasks he was working on.

Startups For the Rest of Us
Episode 762 | Doing Great Work, Hierarchy of SaaS Skills, and Public Deadlines (A Rob Solo Adventure)

So we jumped into a conference room and it was just like panic DEF CON 5 type thing. And it was Derek, myself, and I believe it was Anna, who was our customer success person. And we said, what do we need to change? And we spent like an hour just hashing out, what can we do to make this work? And then we pulled in a different engineer, Ian, off of the tasks he was working on.

Startups For the Rest of Us
Episode 762 | Doing Great Work, Hierarchy of SaaS Skills, and Public Deadlines (A Rob Solo Adventure)

And Derek set to get in designing. And we were like, we really want to hit this deadline. We could push the deadline out, obviously. I don't actually know how many people would notice. You know, there's always that. Think of you're paying more attention to your deadlines than other people are. But it was stressful. And I remember thinking, I'm never doing this again. In the end, we made it.

Startups For the Rest of Us
Episode 762 | Doing Great Work, Hierarchy of SaaS Skills, and Public Deadlines (A Rob Solo Adventure)

And Derek set to get in designing. And we were like, we really want to hit this deadline. We could push the deadline out, obviously. I don't actually know how many people would notice. You know, there's always that. Think of you're paying more attention to your deadlines than other people are. But it was stressful. And I remember thinking, I'm never doing this again. In the end, we made it.

Startups For the Rest of Us
Episode 762 | Doing Great Work, Hierarchy of SaaS Skills, and Public Deadlines (A Rob Solo Adventure)

We got onboarding redone and everything was fine. It was a stressful couple weeks. So the lesson is not I'll never do that again. But I think the level of rigor that I had at the time about dotting on the I's and crossing all the T's was not enough that I could call my shot like this.

Startups For the Rest of Us
Episode 762 | Doing Great Work, Hierarchy of SaaS Skills, and Public Deadlines (A Rob Solo Adventure)

We got onboarding redone and everything was fine. It was a stressful couple weeks. So the lesson is not I'll never do that again. But I think the level of rigor that I had at the time about dotting on the I's and crossing all the T's was not enough that I could call my shot like this.

Startups For the Rest of Us
Episode 762 | Doing Great Work, Hierarchy of SaaS Skills, and Public Deadlines (A Rob Solo Adventure)

Because if you're going to do this, you need, I think, to have checklists and sanity checks and double checks and probably a few brainstorming conversations. Just thinking through, if I'm going to commit to this, have I thought of everything? Because really we hadn't. We'd forgotten this thing. And it was the one time that we really committed to something.

Startups For the Rest of Us
Episode 762 | Doing Great Work, Hierarchy of SaaS Skills, and Public Deadlines (A Rob Solo Adventure)

Because if you're going to do this, you need, I think, to have checklists and sanity checks and double checks and probably a few brainstorming conversations. Just thinking through, if I'm going to commit to this, have I thought of everything? Because really we hadn't. We'd forgotten this thing. And it was the one time that we really committed to something.

Startups For the Rest of Us
Episode 762 | Doing Great Work, Hierarchy of SaaS Skills, and Public Deadlines (A Rob Solo Adventure)

So I think there are a couple takeaways here. Number one, public deadlines can be helpful. But I think if you're going to commit to one, that you need to be pretty damn sure that you have thought of everything. And so the big mistake I think we made was not committing to the public deadline, but I think it was not being rigorous enough with thinking through everything that needed to happen there.

Startups For the Rest of Us
Episode 762 | Doing Great Work, Hierarchy of SaaS Skills, and Public Deadlines (A Rob Solo Adventure)

So I think there are a couple takeaways here. Number one, public deadlines can be helpful. But I think if you're going to commit to one, that you need to be pretty damn sure that you have thought of everything. And so the big mistake I think we made was not committing to the public deadline, but I think it was not being rigorous enough with thinking through everything that needed to happen there.

Startups For the Rest of Us
Episode 762 | Doing Great Work, Hierarchy of SaaS Skills, and Public Deadlines (A Rob Solo Adventure)

But the other thing that I would say is, I don't know that public deadlines are that necessary in most cases. I think internal deadlines can definitely be helpful for everyone working towards a thing, especially if you have multiple teams, you know, you have sales and customer success and support who all need to be on board and trained up on a feature of course.

Startups For the Rest of Us
Episode 762 | Doing Great Work, Hierarchy of SaaS Skills, and Public Deadlines (A Rob Solo Adventure)

But the other thing that I would say is, I don't know that public deadlines are that necessary in most cases. I think internal deadlines can definitely be helpful for everyone working towards a thing, especially if you have multiple teams, you know, you have sales and customer success and support who all need to be on board and trained up on a feature of course.

Startups For the Rest of Us
Episode 762 | Doing Great Work, Hierarchy of SaaS Skills, and Public Deadlines (A Rob Solo Adventure)

At that point, you got to have some type of concrete deadline. But I think people also over-index on specifically public deadlines. and perhaps overuse them because we certainly function quite well without them for a long time. So that wraps up this episode of Startups for the Rest of Us.

Startups For the Rest of Us
Episode 762 | Doing Great Work, Hierarchy of SaaS Skills, and Public Deadlines (A Rob Solo Adventure)

At that point, you got to have some type of concrete deadline. But I think people also over-index on specifically public deadlines. and perhaps overuse them because we certainly function quite well without them for a long time. So that wraps up this episode of Startups for the Rest of Us.

Startups For the Rest of Us
Episode 762 | Doing Great Work, Hierarchy of SaaS Skills, and Public Deadlines (A Rob Solo Adventure)

Hope you enjoyed a little walk down memory lane, as well as some thoughts on Paul Graham essays and Twitter X conversations. This is Rob Walling, signing off from episode 762.

Startups For the Rest of Us
Episode 762 | Doing Great Work, Hierarchy of SaaS Skills, and Public Deadlines (A Rob Solo Adventure)

Hope you enjoyed a little walk down memory lane, as well as some thoughts on Paul Graham essays and Twitter X conversations. This is Rob Walling, signing off from episode 762.

Startups For the Rest of Us
Episode 761 | TinySeed Tales s4e7: Identifying Pain Points

Welcome back to Season 4, Episode 7 of Tiny Seed Tales, where we continue hearing Colleen Schnettler's startup journey as she ventures on now as a solo founder. Before we get into the episode, if you are a SaaS founder, doing at least $1 million in ARR aren't going to be there soon. You should check out SaaSInstitute.com.

Startups For the Rest of Us
Episode 761 | TinySeed Tales s4e7: Identifying Pain Points

Welcome back to Season 4, Episode 7 of Tiny Seed Tales, where we continue hearing Colleen Schnettler's startup journey as she ventures on now as a solo founder. Before we get into the episode, if you are a SaaS founder, doing at least $1 million in ARR aren't going to be there soon. You should check out SaaSInstitute.com.

Startups For the Rest of Us
Episode 761 | TinySeed Tales s4e7: Identifying Pain Points

That's our premium coaching program for founders doing seven and eight figures. We have our first two coaches in place, Jordan Gall, who many of you know from Bootstrapped Web, founder of CartHook, founder of Rosie, as well as Mark Thomas, who runs growth at Podia and formerly worked at Powered by Search.

Startups For the Rest of Us
Episode 761 | TinySeed Tales s4e7: Identifying Pain Points

That's our premium coaching program for founders doing seven and eight figures. We have our first two coaches in place, Jordan Gall, who many of you know from Bootstrapped Web, founder of CartHook, founder of Rosie, as well as Mark Thomas, who runs growth at Podia and formerly worked at Powered by Search.